What if no one wants to pay it, does Iggy just walk and you guys are stuck with nothing? There's a possibility that the market could change especially if there's an influx of talent and the value of players descending. Especially in the case of Iggy, since he basically has 2 or 3 teams that he would even consider getting traded to.

Yes - but from a PR perspective it's possibly better for the team if he walks at the end of the year.

If Iginla wants to leave and decides to go at the end of the season, the team can at least spin the fact they tried to build a winner around him and it didn't work out and Iginla chose to head elsewhere.

If they actively trade the face of the franchise for peanuts it's hard to justify.